WO2015100198A1 - Compositions durcissables à l'humidité - Google Patents

Compositions durcissables à l'humidité Download PDF

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Publication number
WO2015100198A1
WO2015100198A1 PCT/US2014/071804 US2014071804W WO2015100198A1 WO 2015100198 A1 WO2015100198 A1 WO 2015100198A1 US 2014071804 W US2014071804 W US 2014071804W WO 2015100198 A1 WO2015100198 A1 WO 2015100198A1
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WIPO (PCT)
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groups
composition
weight
polymer
group
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PCT/US2014/071804
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English (en)
Inventor
Frederic Gubbels
David M. HAGAN
Angela L. STRINGER
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Dow Corning Corporation
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Priority to KR1020167019483A priority Critical patent/KR101823857B1/ko
Priority to JP2016542178A priority patent/JP6522625B2/ja
Priority to US15/107,181 priority patent/US10308838B2/en
Priority to CA2933245A priority patent/CA2933245A1/fr
Priority to EP14827362.6A priority patent/EP3087150A1/fr
Priority to CN201480070721.8A priority patent/CN105849213B/zh
Publication of WO2015100198A1 publication Critical patent/WO2015100198A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/06—Preparatory processes
    • C08G77/08—Preparatory processes characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

Definitions

  • compositions cured by the reaction of hydroxyl or hydrolysable groups bonded to silicon.
  • Such compositions generally comprising a polymer containing reactive hydroxyl or hydrolysable groups bonded to silicon and a crosslinking agent containing groups reactive with the reactive groups of the polymer in the presence of moisture, are used for example as ambient temperature curable sealants or coatings.
  • compositions are typically either prepared in the form of one-part compositions curable upon exposure to atmospheric moisture at room temperature or multiple (typically two) part compositions curable upon mixing at room temperature.
  • sealant compositions In use as a sealant, it is important that the composition has a blend of properties which render it capable of being applied as a paste to a joint between substrate surfaces where it can be worked, prior to curing, to provide a smooth surfaced mass which will remain in its allotted position until it has cured into an elastomeric body adherent to the adjacent substrate surfaces.
  • sealant compositions are designed to cure quickly enough to provide a sound seal within several hours but at a speed enabling the applied material to be tooled into a desired configuration shortly after application.
  • the moisture curable compositions generally contain an organometallic compound as a catalyst for the reaction of the reactive groups of the polymer with the crosslinking agent. Although these groups react in the presence of moisture without a catalyst, an organometallic compound catalyst is generally required to promote cure of the composition, especially surface cure, in an acceptably short time. These organometallic compounds can be problematic for human health and the environment. Tin compounds, particularly diorganotin compounds such as dibutyltin dilaurate and dibutyltin diacetate, have been the most widely used catalysts for curing these moisture curable compositions, but there are now concerns about their continued use on health and environmental grounds.
  • silanes may function as a cure catalyst avoiding or minimising the need for traditionally used condensation cure catalysts.
  • a moisture curable composition comprising (A) a polymer containing reactive hydroxyl or hydrolysable groups bonded to silicon which groups are reactive in the presence of moisture,
  • crosslinking agent comprising at least two and preferably at least three groups reactive with the silicon-bonded hydroxyl or hydrolysable groups of polymer (A),
  • R and R 2 are alkoxy groups containing from 1 to 6 carbons
  • ⁇ Y and Y 2 are alkyl groups containing from 1 to 8 carbons
  • Z and Z 2 are alkylene groups having from 1 to 12 carbons
  • G is a chemical group containing a heteroatom with a lone pair of electron
  • silane (D) is provided to function as the cure catalyst.
  • organometallic compound type catalyst e.g. tin based catalyst is required for compositions as herein described to cure.
  • a polymer base comprising components (A) and (C) and a cure package comprising components (B) and (D) in amounts such that when combined the composition will comprise from 1 to 15 parts by weight of polymer base per 1 part by weight of the cure package.
  • the polymer (A) is a polysiloxane containing polymer containing at least two hydroxyl or hydrolysable groups, preferably terminal hydroxyl or hydrolysable groups.
  • the polymer can for example have the general formula:
  • X 1 and X 2 are independently selected from silicon containing groups which contain hydroxyl or hydrolysable substituents and A' represents a polymer chain.
  • Examples of X 1 or X 2 groups incorporating hydroxyl and/or hydrolysable substituents include groups terminating as described below:
  • each R a independently represents a monovalent hydrocarbyl group, for example, an alkyl group, in particular having from 1 to 8 carbon atoms, (and is preferably methyl); each R b and R d group is independently an alkyl or alkoxy group in which the alkyl groups suitably have up to 6 carbon atoms; R c is a divalent hydrocarbon group which contains between 1 and 10 carbon atoms which may be interrupted by one or more siloxane spacers having up to six silicon atoms; and p has the value 0, 1 or 2.
  • the polymer chain A' can for example be a siloxane-containing polymer chain such as an organopolysiloxane or a siloxane/organic block copolymeric molecular chain.
  • the polymer (A) preferably includes siloxane units of formula (2):
  • each R 5 is independently an organic group such as a hydrocarbon group having from 1 to 18 carbon atoms, a substituted hydrocarbon group having from 1 to 18 carbon atoms or a hydrocarbonoxy group having up to 18 carbon atoms and s has, on average, a value of from 1 to 3, preferably 1 .8 to 2.2.
  • a substituted hydrocarbon group one or more hydrogen atoms in the group have been replaced with another substituent.
  • substituents include, but are not limited to, halogen atoms such as chlorine, fluorine, bromine, and iodine; halogen atom containing groups such as chloromethyl, perfluorobutyl, trifluoroethyl, and nonafluorohexyl; oxygen atoms; oxygen atom containing groups such as (meth)acrylic and carboxyl; nitrogen atoms; nitrogen atom containing groups such as amino-functional groups, amido-functional groups, and cyano-functional groups; sulphur atoms; and sulphur atom containing groups such as mercapto groups.
  • halogen atoms such as chlorine, fluorine, bromine, and iodine
  • halogen atom containing groups such as chloromethyl, perfluorobutyl, trifluoroethyl, and nonafluorohexyl
  • oxygen atoms oxygen atom containing groups such as (meth)acrylic and carboxyl
  • each R 5 is a hydrocarbyl group having from 1 to 10 carbon atoms optionally substituted with one or more halogen group such as chlorine or fluorine and s is 0, 1 or 2.
  • groups R 5 include methyl, ethyl, propyl, butyl, vinyl, cyclohexyl, phenyl, tolyl group, a propyl group substituted with chlorine or fluorine such as 3,3,3-trifluoropropyl, chlorophenyl, beta-(perfluorobutyl)ethyl or chlorocyclohexyl group.
  • at least some and preferably substantially all of the groups R 5 are methyl.
  • the polymer (A), particularly if it is a polydiorganosiloxane, may have a viscosity of up to 1 ,000,000 mPa.s at 25°C. All viscosity values provided are measured using a Brookfield ® viscometer using a DV-2 THB RV/MA/HB-3 spindle and all viscosity
  • Polydiorganosiloxanes comprising units of the formula (2) may be homopolymers or copolymers in either block form or in a random continuation. Mixtures of different polydiorganosiloxanes are also suitable.
  • At least one block will comprise siloxane units in which both R 5 groups are alkyl groups.
  • the polymer (A) may alternatively have a block copolymeric backbone comprising at least one block of siloxane groups of the type depicted in formula (2) above and at least one block comprising any suitable organic polymer chain.
  • the organic polymer backbone may comprise, for example, polyoxyalkylene, polystyrene and/or substituted polystyrenes such as poly(a-methylstyrene), poly(vinylmethylstyrene), dienes, poly(p-trimethylsilylstyrene) and poly(p-trimethylsilyl-a-methylstyrene).
  • organic components which may be incorporated in the polymeric backbone may include acetylene terminated oligophenylenes, vinylbenzyl terminated aromatic polysulphones oligomers, aromatic polyesters, aromatic polyester based monomers, polyalkylenes, polyurethanes, aliphatic polyesters, aliphatic polyamides and aromatic polyamides.
  • the most preferred organic polymer blocks in a siloxane organic block copolymer (A) are polyoxyalkylene based blocks comprising recurring oxyalkylene units, illustrated by the average formula (-C n H 2 n-0-) y wherein n is an integer from 2 to 4 inclusive and y is an integer of at least four.
  • the number average molecular weight of each polyoxyalkylene polymer block may range from about 300 to about 10,000.
  • the oxyalkylene units are not necessarily identical throughout the polyoxyalkylene block, but can differ from unit to unit.
  • a polyoxyalkylene block for example, can comprise oxyethylene units (-C 2 H 4 -0-), oxypropylene units (-C 3 H 6 -0-) or oxybutylene units (-C 4 H 8 -0-), or mixtures thereof.
  • polyoxyalkylene polymeric backbone consists essentially of oxyethylene units or oxypropylene units.
  • Other polyoxyalkylene blocks may include for example: units of the structure-
  • each R e is the same or different and is a divalent hydrocarbon group having 2 to 8 carbon atoms
  • each R f is the same or different and is an ethylene group or propylene group
  • each R 9 is the same or different and is a hydrogen atom or methyl group and each of the subscripts h and q1 is a positive integer in the range from 3 to 30.
  • the polymer (A) can alternatively be an organic polymer containing reactive hydroxyl or hydrolysable groups bonded to silicon.
  • an organic polymer we mean a material based on carbon chemistry, which is a polymer in which at least half the atoms in the polymer backbone are carbon atoms.
  • the organic polymer is preferably a telechelic polymer having terminal moisture curable silyl groups containing reactive hydroxyl or hydrolysable groups bonded to silicon.
  • the organic polymer can for example be selected from polyethers, hydrocarbon polymers, acrylate polymers, polyurethanes and polyureas.
  • polyether is a polyoxyalkylene polymer comprising recurring oxyalkylene units of the formula (-C n H 2n -0-) wherein n is an integer from 2 to 4 inclusive, as described above in connection with siloxane polyoxyalkylene block copolymers.
  • Polyoxyalkylenes usually have terminal hydroxyl groups and can readily be terminated with moisture curable silyl groups, for example by reaction with an excess of an
  • alkyltrialkoxysilane to introduce terminal alkyldialkoxysilyl groups.
  • Polymerization may occur via a hydrosilylation type process.
  • Polyoxyalkylenes consisting wholly or mainly of oxypropylene units have properties suitable for many sealant uses.
  • Polyoxyalkylene polymers, particularly polyoxypropylenes, having terminal alkyldialkoxysilyl or trialkoxysilyl groups may be particularly suitable for use as a polymer (A) having reactive groups which react with each other in the presence of moisture and which do not need a separate crosslinking agent (B) in the composition.
  • silyl modified hydrocarbon polymers examples include silyl modified
  • Silyl modified polyisobutylene which is available commercially in the form of telechelic polymers.
  • Silyl modified polyisobutylene can for example contain curable silyl groups derived from a silyl- substituted alkyl acrylate or methacrylate monomer such as a dialkoxyalkylsilylpropyl methacrylate or trialkoxysilylpropyl methacrylate, which can be reacted with a
  • polyisobutylene prepared by living anionic polymerization, atom transfer radical
  • the organic polymer having hydrolysable silyl groups can alternatively be an acrylate polymer, that is an addition polymer of acrylate and/or methacrylate ester monomers, which preferably comprise at least 50% by weight of the monomer units in the acrylate polymer.
  • acrylate ester monomers are n-butyl, isobutyl, n-propyl, ethyl, methyl, n-hexyl, n-octyl and 2-ethylhexyl acrylates.
  • methacrylate ester monomers are n-butyl, isobutyl, methyl, n-hexyl, n-octyl, 2-ethylhexyl and lauryl
  • the acrylate polymer preferably has a glass transition temperature (Tg) below ambient temperature; acrylate polymers are generally preferred over methacrylates since they form lower Tg polymers. Polybutyl acrylate is particularly preferred.
  • the acrylate polymer can contain lesser amounts of other monomers such as styrene, acrylonitrile or acrylamide.
  • the acrylate(s) can be polymerized by various methods such as conventional radical polymerization, or living radical polymerization such as atom transfer radical polymerization, reversible addition-fragmentation chain transfer
  • the curable silyl groups can for example be derived from a silyl-substituted alkyl acrylate or methacrylate monomer.
  • Hydrolysable silyl groups such as dialkoxyalkylsilyl or trialkoxysilyl groups can for example be derived from a dialkoxyalkylsilylpropyl methacrylate or trialkoxysilylpropyl methacrylate.
  • the acrylate polymer When the acrylate polymer has been prepared by a polymerization process which forms reactive terminal groups, such as atom transfer radical polymerization, chain transfer polymerization, or living anionic polymerization, it can readily be reacted with the silyl-substituted alkyl acrylate or methacrylate monomer to form terminal hydrolysable silyl groups.
  • reactive terminal groups such as atom transfer radical polymerization, chain transfer polymerization, or living anionic polymerization
  • Silyl modified polyurethanes or polyureas can for example be prepared by the reaction of polyurethanes or polyureas having terminal ethylenically unsaturated groups with a silyl monomer containing hydrolysable groups and a Si-H group, for example a dialkoxyalkylsilicon hydride or trialkoxysilicon hydride.
  • the polymer may comprise a diorganopolysiloxane having a viscosity in the range of 20 to 1 ,000,000 mPa-s at 25 Q C having: 20 to 100 parts by weight of a diorganopolysiloxane (A-1 ) capped at both molecular terminals with alkoxysilyl groups or hydroxysilyl groups, and 0 to 80 parts by weight of a diorganopolysiloxane (A-2) capped at one molecular terminal with an alkoxysilyl group or a hydroxysilyl group and capped at the other molecular terminal with an alkyl group or an alkenyl group.
  • A-1 diorganopolysiloxane
  • A-2 diorganopolysiloxane
  • (A-1 ) and (A-2) are present in a (A-1 ):(A-2) weight ratio of from 100:0 to 20:80, alternatively (A-1 ):(A- 2) from 100:0 to 60:40, and further alternatively from 100:0 to 80:20.
  • the constituents (A-1 ) and (A-2) have viscosities in the range of 20 to 1 ,000,000 mPa-s, alternatively in the range of 100 to 500,000 mPa-s, at 25 Q C, alternatively in the range of 100 to 100,000 mPa-s, at 25 Q Cin each case, as mentioned above, measured using a Brookfield ® viscometer using a DV-2 THB RV/MA/HB-3 spindle.
  • the crosslinker (B) contains at least two, alternatively at least three groups reactive with the silicon-bonded hydroxyl or hydrolysable groups of polymer (A).
  • the reactive groups of crosslinker (B) are themselves preferably silanol groups or silicon bonded hydrolysable groups, most preferably hydrolysable groups.
  • the cross-linker can for example be a silane or short chain organopolysiloxane, for example a
  • crosslinker (B) can alternatively be an organic polymer substituted by silicon-bonded hydrolysable groups.
  • cross-linker (B) has a structure which does not fall within the scope of silane D.
  • the hydrolysable groups in the crosslinker can for example be selected from acyloxy groups (for example, acetoxy, octanoyloxy, and benzoyloxy groups); ketoximino groups (for example dimethyl ketoximo, and isobutylketoximino); alkoxy groups (for example methoxy, ethoxy, and propoxy) and/or alkenyloxy groups (for example
  • the crosslinking agent (B) is a silane having three silicon-bonded hydrolysable groups per molecule.
  • the fourth group is suitably a non- hydrolysable silicon-bonded organic group.
  • These silicon-bonded organic groups are suitably hydrocarbyl groups which are optionally substituted by halogen such as fluorine and chlorine.
  • halogen such as fluorine and chlorine.
  • Examples of such fourth groups include alkyl groups (for example methyl, ethyl, propyl, and butyl); cycloalkyl groups (for example cyclopentyl and cyclohexyl);
  • alkenyl groups for example vinyl and allyl
  • aryl groups for example phenyl, and tolyl
  • aralkyi groups for example 2-phenylethyl
  • the fourth silicon- bonded organic group is methyl or ethyl.
  • crosslinking agents (B) include acyloxysilanes, particularly
  • acetoxysilanes such as methyltriacetoxysilane, vinyltriacetoxysilane, ethyl triacetoxysilane, di-butoxy diacetoxysilane and/or dimethyltetraacetoxydisiloxane, and also phenyl- tripropionoxysilane.
  • the crosslinking agent can be an oxime-functional silane such as methyltris(methylethylketoximo)silane, vinyl-tris(methylethylketoximo)silane, or an alkoxytrioximosilane.
  • the crosslinking agent can be an alkoxysilane, for example an alkyltrialkoxysilane such as methyltrimethoxysilane, methyltriethoxysilane,
  • the crosslinking agent can alternatively be a short chain polydiorganosiloxane, for example polydimethylsiloxane, with trimethoxysilyl terminal groups or can be an organic polymer, for example a polyether such as a polypropylene oxide with terminal groups having methoxysilane functionality such as trimethoxysilyl groups.
  • the cross-linker used may also comprise any combination of two or more of the above.
  • cross-linkers include alkylalkenylbis(N-alkylacetamido) silanes such as methylvinyldi-(N-methylacetamido)silane, and methylvinyldi-(N- ethylacetamido)silane; dialkylbis(N-arylacetamido) silanes such as dimethyldi-(N- methylacetamido)silane; and dimethyldi-(N-ethylacetamido)silane; alkylalkenylbis(N- arylacetamido) silanes such as methylvinyldi(N-phenylacetamido)silane and dialkylbis(N- arylacetamido) silanes such as dimethyldi-(N-phenylacetamido)silane, or any combination of two or more of the above.
  • cross-linker (B) has only
  • compositions suitably contain crosslinker (B) in at least a stoichiometric amount as compared to the polymer (A).
  • Compositions may contain, for example, from 1 -30% by weight of crosslinker (B), generally from 1 to 10%.
  • cross-linkers (B) containing acetoxy groups or oximino groups may typically be present in amounts of from 3 to 8 % by weight of the composition.
  • the filler (C) can for example be a reinforcing filler, which will improve the mechanical properties of the composition, such as high surface area fumed and precipitated silicas and to a degree precipitated calcium carbonate, and/or can comprise a non-reinforcing filler such as crushed quartz, ground calcium carbonate, diatomaceous earth, barium sulphate, iron oxide, titanium dioxide, carbon black, talc, crystobalite, mica, feldspar or wollastonite.
  • a reinforcing filler such as crushed quartz, ground calcium carbonate, diatomaceous earth, barium sulphate, iron oxide, titanium dioxide, carbon black, talc, crystobalite, mica, feldspar or wollastonite.
  • fillers which might be used alone or in addition to the above include aluminite, calcium sulphate (anhydrite), gypsum, magnesium carbonate, aluminium trihydroxide, magnesium hydroxide (brucite), graphite, copper carbonate, e.g. malachite, nickel carbonate, barium carbonate, strontium carbonate, aluminium oxide, or silicates from the group consisting of the olivine group, the garnet group, aluminosilicates, ring silicates, chain silicates and sheet silicates, or plastic or glass microspheres, preferably hollow microspheres.
  • the filler when present in the composition may be present in a preferred range of 3 to 400 parts by weight per 100 parts of polymer (A) of the moisture curable composition. Typically when filler is present at least some filler in the composition will be reinforcing.
  • a surface treatment of the filler(s) may be performed, for example with a fatty acid or a fatty acid ester such as a stearate, or with organosilanes, organosiloxanes, or organosilazanes hexaalkyl disilazane or short chain siloxane diols to render the filler(s) hydrophobic and therefore easier to handle and obtain a homogeneous mixture with the other sealant components
  • the surface treatment of the fillers makes the fillers e.g. ground calcium carbonate and/or precipitated calcium carbonate easily wetted by the silicone polymer. These surface modified fillers do not clump, and can be homogeneously incorporated into the silicone polymer.
  • the surface treated fillers give a lower conductivity than untreated or raw material.
  • the filler(s) (C) may for example be precipitated silica, ground calcium carbonate and/or precipitated calcium carbonate each of which has independently been treated by a treating agent discussed above, typically stearic acid or a stearate.
  • filler content of the composition will reside within the range from about 5 to about 800 parts by weight, preferably from 25 to 400 parts by weight per 100 parts by weight of polymer A.
  • Silane (D), as hereinbefore described has the following structure:
  • R and R 2 are alkoxy groups containing from 1 to 6 carbons
  • Y and Y 2 are alkyl groups containing from 1 to 8 carbons
  • Z and Z 2 are alkylene groups having from 1 to 12 carbons
  • G and G 2 are chemical groups containing a heteroatom with a lone pair of electrons.
  • Each R and R 2 may be the same or different and have from 1 to 6 carbons and
  • each R and R 2 contains 1 to 3 carbons.
  • each R and R 2 is either a methoxy group or an ethoxy group.
  • Y and Y 2 are linear or branched alkyl groups containing from 1 to 8 carbons, alternatively containing 1 to 6 carbon atoms
  • Each of Z and Z 2 may be the same or different and are linear or branched alkylene groups having from 1 to 12 carbons, alternatively linear or branched alkylene groups having from 1 to 6 carbons, further alternatively linear alkylene groups containing 2 to 4 carbon atoms.
  • G is a chemical group containing a heteroatom with a lone pair of electrons such as a secondary amine or a substituted urea group.
  • the subscripts m and q are independently 1 , 2 or 3, alternatively 2 or 3.
  • Silane, (D) examples include:
  • silane D is selected from bis(triethoxysilylpropyl)amine
  • the composition of the invention can include other ingredients known for use in moisture curable compositions based on silicon-bonded hydroxyl or hydrolysable groups such as sealant compositions.
  • the composition may comprise a silicone or organic fluid which is not reactive with polymer (A) or crosslinking agent (B).
  • a silicone or organic fluid acts as a plasticizer or extender (sometimes referred to as a processing aid) in the composition.
  • the silicone or organic fluid can be present in up to 200 parts by weight of the moisture curable composition per 100 parts of polymer (A), for example from 5 or 10 parts by weight up to 150 parts by weight based on 100 parts by weight of polymer (A).
  • non-reactive silicone fluids useful as plasticizers include silicone oils, plasticizers, and silicone oils.
  • polydiorganosiloxanes such as polydimethylsiloxane having terminal triorganosiloxy groups wherein the organic substituents are, for example, methyl, vinyl or phenyl or combinations of these groups.
  • Such polydimethylsiloxanes can for example have a viscosity of from about 5 to about 100,000 mPa.s at 25°C.
  • compatible organic plasticisers which can be used additionally to or instead of the silicone fluid plasticiser include dialkyl phthalates wherein the alkyl group may be linear and/or branched and contains from six to 20 carbon atoms such as dioctyl, dihexyl, dinonyl, didecyl, diallanyl and other phthalates, and analogous adipate, azelate, oleate and sebacate esters; polyols such as ethylene glycol and its derivatives; and organic phosphates such as tricresyl phosphate and/or triphenyl phosphates.
  • dialkyl phthalates wherein the alkyl group may be linear and/or branched and contains from six to 20 carbon atoms such as dioctyl, dihexyl, dinonyl, didecyl, diallanyl and other phthalates, and analogous adipate, azelate, oleate and sebacate esters
  • extenders for use in compositions according to the invention include mineral oil based (typically petroleum based) paraffinic hydrocarbons, mixtures of paraffinic and naphthenic hydrocarbons, paraffin oils comprising cyclic paraffins and non-cyclic paraffins and hydrocarbon fluids containing naphthenics, polycyclic naphthenics and paraffins, or polyalkylbenzenes such as heavy alkylates (alkylated aromatic materials remaining after distillation of oil in a refinery). Examples of such extenders are discussed in GB2424898 the content of which is hereby enclosed by reference.
  • Such a hydrocarbon extender can for example have an ASTM D 86-09 boiling point of from 235°C to 400°C.
  • An example of a preferred organic extender is the hydrocarbon fluid sold by Total under the trade mark Hydroseal ® G250H.
  • the extender or plasticiser may alternatively comprise one or more non-mineral based natural oil, i.e. an oil derived from animals, seeds or nuts and not from petroleum, or a derivative thereof such as a transesterified vegetable oil, a boiled natural oil, a blown natural oil, or a stand oil (thermally polymerized oil).
  • compositions include but are not restricted to rheology modifiers; adhesion promoters, pigments, heat stabilizers, flame retardants, UV stabilizers, chain extenders, cure modifiers, electrically and/or heat conductive fillers, and fungicides and/or biocides and the like.
  • the rheology modifiers include silicone organic co-polymers such as those described in EP 0802233 based on polyols of polyethers or polyesters; non-ionic surfactants selected from the group consisting of polyethylene glycol, polypropylene glycol, ethoxylated castor oil, oleic acid ethoxylate, alkylphenol ethoxylates, copolymers or ethylene oxide and propylene oxide, and silicone polyether copolymers; as well as silicone glycols.
  • these rheology modifiers particularly copolymers of ethylene oxide and propylene oxide, and silicone polyether copolymers, may enhance the adhesion of the sealant to substrates, particularly plastic substrates.
  • adhesion promoters which may be incorporated in moisture curable compositions according to the invention include alkoxysilanes such as aminoalkylalkoxysilanes, for example 3-aminopropyltriethoxysilane,
  • epoxyalkylalkoxysilanes for example, 3-glycidoxypropyltrimethoxysilane and, mercapto- alkylalkoxysilanes, and reaction products of ethylenediamine with silylacrylates.
  • Isocyanurates containing silicon groups such as 1 ,3,5-tris(trialkoxysilylalkyl) isocyanurates may additionally be used.
  • Further suitable adhesion promoters are reaction products of epoxyalkylalkoxysilanes such as 3-glycidoxypropyltrimethoxysilane with amino-substituted alkoxysilanes such as 3-aminopropyltrimethoxysilane and optionally with alkylalkoxysilanes such as methyltrimethoxysilane.
  • Chain extenders may include difunctional silanes which extend the length of the polysiloxane polymer chains before cross linking occurs and, thereby, reduce the modulus of elongation of the cured elastomer. Chain extenders and crosslinkers compete in their reactions with the functional polymer ends; in order to achieve noticeable chain extension, the difunctional silane must have substantially higher reactivity than the trifunctional crosslinker with which it is used.
  • Suitable chain extenders include diamidosilanes such as dialkyldiacetamidosilanes or alkenylalkyldiacetamidosilanes, particularly methylvinyldi(N- methylacetamido)silane, or dimethyldi(N-methylacetamido)silane, diacetoxysilanes such as dialkyldiacetoxysilanes or alkylalkenyldiacetoxysilanes, diaminosilanes such as
  • dialkyldiaminosilanes or alkylalkenyldiaminosilanes, dialkoxysilanes such as
  • alkylalkenyldiketoximinosilanes alkylalkenyldiketoximinosilanes.
  • Electrically conductive fillers may include carbon black, metal particles such as silver particles any suitable electrically conductive metal oxide fillers such as titanium oxide powder whose surface has been treated with tin and/or antimony, potassium titanate powder whose surface has been treated with tin and/or antimony, tin oxide whose surface has been treated with antimony, and zinc oxide whose surface has been treated with aluminium.
  • Thermally conductive fillers may include metal particles such as powders, flakes and colloidal silver, copper, nickel, platinum, gold aluminium and titanium, metal oxides, particularly aluminium oxide (Al 2 0 3 ) and beryllium oxide (BeO); magnesium oxide, zinc oxide, zirconium oxide.
  • Pigments are utilised to colour the composition as required. Any suitable pigment may be utilised providing it is compatible with the composition. In two part compositions pigments and/or coloured (non-white) fillers e.g. carbon black may be utilised typically in one part of the composition and may be relied upon to show good mixing of the different parts prior to application.
  • coloured (non-white) fillers e.g. carbon black
  • Biocides may additionally be utilized in the composition if required. It is intended that the term “biocides” includes bactericides, fungicides and algicides, and the like.
  • compositions as described herein include, for the sake of example:
  • Carbamates such as methyl-N-benzimidazol-2-ylcarbamate (carbendazim) and other suitable carbamates, 10,10'-oxybisphenoxarsine, 2-(4-thiazolyl)-benzimidazole,
  • DCOIT 4,5-dichloro-2-(n-octyl)-4-isothiazolin-3-one
  • OIT 2-(n- octyl)-4-isothiazolin-3-one
  • BBIT n-butyl-1 ,2-benzisothiazolin-3-one
  • biocides might include for example Zinc Pyridinethione, 1 -(4-Chlorophenyl)-4,4-dimethyl-3- (1 ,2,4-triazol-1 -ylmethyl)pentan-3-ol and/or 1 -[[2-(2,4-dichlorophenyl)-4-propyl-1 ,3- dioxolan-2-yl] methyl]-1 H-1 ,2,4-triazole.
  • the fungicide and/or biocide may suitably be present in an amount of from 0 to 0.3% by weight of the composition and may be present in an encapsulated form where required such as described in EP2106418.
  • compositions typically the composition comprises 30 to 70 weight % of polymer (A) containing reactive hydroxyl or hydrolysable groups bonded to silicon which groups are reactive in the presence of moisture 0.5 - 10 weight % of crosslinking agent (B) comprising at least two and preferably at least three groups reactive with the silicon-bonded hydroxyl or hydrolysable groups of polymer (A).
  • crosslinking agent B
  • B crosslinking agent
  • C reinforcing or semi-reinforcing fillers
  • D silane
  • Such compositions do not require a standard condensation catalyst because silane (D) functions as the catalyst.
  • a base composition comprising: 30 to 70 weight% of polymer (A) containing reactive hydroxyl or hydrolysable groups bonded to silicon which groups are reactive in the presence of moisture and 30 to 70 weight % of one or more reinforcing or semi-reinforcing fillers (C). Suitable additives as hereinbefore described may also be present and the base composition composition total to 100 weight % of the base composition; and a cross-linking composition, comprising:
  • crosslinking agent (B) comprising at least two and preferably at least three groups reactive with the silicon-bonded hydroxyl or hydrolysable groups of polymer (A) and silane (D) as hereinbefore described in a ratio of (B) : (D) of between 1 : 9 and 9 : 1 , alternatively between 3 : 7 and 7 : 3, alternatively between 2 : 3 and 3 : 2.
  • the Crosslinking part may additionally comprise one or more polymers (E) unreactive with components (B) and (D) and/or a pigment or coloured filler (F).
  • the unreactive polymer functions as a plasticiser or extender and is selected from polydimethylsiloxane having terminal triorganosiloxy groups wherein the organic substituents are, for example, methyl, vinyl or phenyl or combinations of these groups.
  • polydimethylsiloxanes can for example have a viscosity of from about 5 to about 100,000 mPa.s at 25°C.
  • organic polymers such as mineral oil based (typically petroleum based) paraffinic hydrocarbons may be used, i.e. mixtures of paraffinic and naphthenic hydrocarbons, paraffin oils comprising cyclic paraffins and non-cyclic paraffins and hydrocarbon fluids containing naphthenics, polycyclic naphthenics and paraffins.
  • composition comprises:
  • a crosslinking agent comprising at least two and preferably at least three groups reactive with the silicon-bonded hydroxyl or hydrolysable groups of polymer (A) and 1 to 50 weight% of silane (D) as hereinbefore described, (E) 5 to 30 weight % of one or more polymers unreactive with (A) or (C); and (F) 1 to 15 weight % of one or more pigments or coloured fillers.
  • the cross-linking composition may contain 0 to 50 weight % of filler (C) depending on the mixing ratio of the two parts of the composition.
  • the ratio of the base composition : cross-linking composition is between 15:1 and 1 :1 , alternatively between 10 : 1 and 1 : 1 . If the intended mixing ratio of base composition : cross-linking composition is 10:1 or greater then no filler (C) will be generally utilized in the cross-linking composition. However if the intended mixing ratio of base composition : cross-linking composition is less than 10:1 than an increasing amount filler (C) will be utilized in the cross-linking composition up to the maximum of 50% if the intended ratio is 1 :1 .
  • the moisture curable compositions can be prepared by mixing the ingredients employing any suitable mixing equipment.
  • preferred one-part moisture curable compositions may be made by mixing polysiloxane (A) with filler (B) and mixing the resulting base with a pre-mix of the crosslinking agent and the dipodal silane.
  • Other additives such as plasticisers and/or extenders, UV stabilizer, pigments and biocides may be added to the mixture at any desired stage.
  • the final mixing step is carried out under substantially anhydrous conditions, and the resulting curable compositions are generally stored under substantially anhydrous conditions, for example in sealed containers, until required for use.
  • each part is mixed together in amounts within the ranges given above and then the base composition and the cross-linker part are inter-mixed in a predetermined ratio e.g. from 15:1 to 1 :1 , alternatively from 12:1 to 5:1 .
  • Such one-part moisture curable compositions according to the invention are stable in storage but cure on exposure to atmospheric moisture produce elastomeric bodies despite not containing the aforementioned metallic catalysts.
  • compositions may be employed in a variety of applications, for example as coating, caulking, mold making and encapsulating materials. They are particularly suitable for sealing joints, cavities and other spaces in articles and structures which are subject to relative movement. They are thus particularly suitable as glazing sealants or adhesives and for sealing building structures where the visual appearance of the sealant is important. They are also useful as insulating glass sealants, structural sealants for building applications. Further applications for the composition hereinbefore described include sealing compositions for electrical/electronic devices, automotive parts and solar modules.
  • compositions are henceforth illustrated by the following Examples, in which parts and percentages are by weight, unless otherwise indicated. All viscosities of starting materials are given as pre-measured values provided by suppliers and viscosity measurements taken during experiments were measured using a Brookfield ® viscometer using a DV-2 THB RV/MA/HB-3 spindle and all viscosity measurements were taken at 25°C unless otherwise indicated.
  • Moisture curable sealant compositions were prepared by mixing the ingredients listed in a Hausschild laboratory mixer (dental mixer) and where required filling the mixed composition into cartridges. [0059] Tables 1 a depicts the composition of the base composition of the 2 part
  • compositions tested in example 1 for their cure properties. It will be noted that, for comparative purposes, as previously indicated the same base composition was used in all samples and comparative samples. Tables 1 b and 1 d provide details of the cross-linking compositions mixed with the equivalently numbered base compositions. The base compositions and the cross-linking compositions were mixed in a ratio of 10 parts by weight of base composition to every 1 part by weight of crosslinking composition.
  • Tables 1 c and 1 e provide details of observations during the cure process of the compositions in Tables 1 a 1 b and 1 c respectively comparing the use of silanes (D) as hereinbefore described as well as non-functional silanes, 1 ,6-Bis(trimethoxysilyl)hexane and 1 ,2- bis(trimethoxysilyl)decane.
  • 1 , 6-Bis(trimethoxysilyl)hexane may be added in current two- part formulations for better durability after hot water adhesion (comp sample 3).
  • the compositions detailed in Table 1 a, 1 b and 1 d involving the aforementioned non-functional silanes used tin II octoate as the catalyst whereas the functional silanes used no catalyst.
  • compositions containing the silanes 1 ,6-Bis(trimethoxysilyl)hexane 1 ,2- bis(trimethoxysilyl)decane failed to cure even in the presence of tin catalysts after 48 hours cure time. (Comp Samples 1 and 4). It must be appreciated that if a two-part sealant composition has not cured after 24 hours there isn't much benefit over a one-part composition which would be expected to cure much slower than the 2 part composition. Sample 1 , comparative sample 2 and Sample 2 again showed better results than Comp Sample 3.
  • Compositions containing Bis[3-trimethoxysilyl) propylethylenediamine and like materials e.g.
  • compositions containing such molecules failed to cure even in the presence of tin catalysts (Comp sample 3).
  • Example 2 focused more on Bis[3-trimethoxysilyl)propylamine and testing of cured properties by durometer, tensile, and elongation of compositions cured with Bis[3- trimethoxysilyl)propylamine. Again throughout Example 2 the same base was used as in Example 1 and as such was not depicted in the following Tables. The cross-linking composition depicted in Tables 2a and 2b were mixed with said base compositions in a ratio of 10 parts base composition to 1 part cross-linking composition.
  • 'Tensile' means tensile strength (breaking stress) in kPa.
  • the tensile tests were performed in accordance with ASTM D412-98a with 3mm sheets after 1 week cure according to ASTM D412-98a.
  • 'Modulus 25%, 50% and 100%' is the nominal stress (or apparent stress, in kPa) at 25%, 50% and 100% elongation respectively. Elongation is given in % according to ASTM D412-98 a for 2 mm sheets.
  • the Hardness was Shore A hardness measured according to ASTM D2240-02b.
  • Table 2c Cured properties of Compositions resulting from the mixture of base compositions with those cross-linking compositions depicted in Table 2a and 2b after 24hrs
  • Table 2d Cured properties of Compositions resulting from the mixture of base compositions with those cross-linking compositions depicted in Table 2a and 2b after 7 days

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Abstract

L'invention concerne une composition durcissable à l'humidité comprenant (A) un polymère contenant des groupes réactifs hydroxyle ou hydrolysables liés à un silicium, groupes qui sont réactifs en présence d'humidité ; (B) un agent de réticulation comprenant au moins deux et de préférence au moins trois groupes réactifs avec les groupes hydroxyle ou hydrolysables liés à un silicium du polymère (A) ; (C) une ou plusieurs charges de renfort et/ou non renforçantes et (D) 15 à 30 % en poids de la composition d'un silane ayant la structure : (R1)m (Y1)3-m Si - Z1 - G1 - Z2 - Si (R2)q (Y2)3-q dans laquelle R1 et R2 sont des groupes alcoxy contenant de 1 à 6 carbones, Y1 et Y2 sont des groupes alkyle contenant de 1 à 8 carbones, Z1 et Z2 sont des groupes alkylène ayant de 1 à 12 carbones, G1 est un groupe chimique contenant un hétéroatome ayant une paire d'électrons solitaire ; et m et q sont indépendamment 1, 2 ou 3. Le silane (D) est conçu pour fonctionner en tant que catalyseur de durcissement.
PCT/US2014/071804 2013-12-23 2014-12-22 Compositions durcissables à l'humidité WO2015100198A1 (fr)

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US10239967B2 (en) 2014-12-12 2019-03-26 Exxonmobil Research And Engineering Company Olefin polymerization catalyst system comprising mesoporous organosilica support
US10351639B2 (en) 2014-12-12 2019-07-16 Exxonmobil Research And Engineering Company Organosilica materials for use as adsorbents for oxygenate removal
US10155826B2 (en) 2014-12-12 2018-12-18 Exxonmobil Research And Engineering Company Olefin polymerization catalyst system comprising mesoporous organosilica support
US10294312B2 (en) 2014-12-12 2019-05-21 Exxonmobil Research And Engineering Company Olefin polymerization catalyst system comprising mesoporous organosilica support
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US10179839B2 (en) 2016-11-18 2019-01-15 Exxonmobil Research And Engineering Company Sulfur terminated organosilica materials and uses thereof
US11319446B2 (en) 2017-07-31 2022-05-03 Dow Silicones Corporation Moisture curable compositions
WO2019102383A1 (fr) * 2017-11-22 2019-05-31 Scg Chemicals Co., Ltd. Polyuréthanes à faible vide
US11111352B2 (en) 2017-12-21 2021-09-07 Exxonmobil Research And Engineering Company Methods of producing organosilica materials and uses thereof

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